Triethylamine → HCID 54310363, compound

A solution of 4-fluorocinnamic acid (2.0 g, 12 mmol), oxalyl chloride (1.65 g, 13 mmol) and N,N-dimethylformamide (four drops) in 40 ml dichloromethane was stirred overnight under nitrogen. The resulting solution was evaporated in vacuo, and the resulting solid redissolved in 10 ml dichloromethane. The resulting solution of 4-fluorocinnamoyl chloride was added dropwise to a cold (5°-10° C.), stirred mixture prepared from N-methylhydroxylamine hydrochloride (1.09 g, 13 mmol) and triethylamine (5 ml, 35 mmol), which had been stirred for 20 minutes. The reaction mixture was allowed to warm to room temperature, then washed successively with aqueous 1N HCl and 1N NaHCO3. The organic solution was then chromatographed on silica gel with 2% isopropanol in dichloromethane. The product was recrystallized from methanol-water, to provide 1.65 g of the titled compound as a white powder, mp 141°-141.5° C.

1. customThe resulting solution was evaporated in vacuo
2. dissolutionthe resulting solid redissolved in 10 ml dichloromethane
3. additionThe resulting solution of 4-fluorocinnamoyl chloride was added dropwise to a cold (5°-10° C.)
4. stirringhad been stirred for 20 minutes
5. washwashed successively with aqueous 1N HCl and 1N NaHCO3
6. customThe organic solution was then chromatographed on silica gel with 2% isopropanol in dichloromethane
7. customThe product was recrystallized from methanol-water

ORD record

ord-84cef7febc054d7897884657847f0ec5

Source dataset

uspto-grants-1989_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04820828